Ingram’s 20 in their Twenties Assembly

PUBLISHED OCTOBER 2025

Demographers tell us that the last cohort of Millennials is now 29, and the stampede of Generation Z into the under-30 work force is nearly complete. The youngest workers among us are starting their careers in a place far different from previous generations: career mobility among them is higher than any previous generation; they’re confronted with lifestyle considerations that are delaying marriage, children and home ownership; their prospects for wealth accumulation and secure retirements are sketchier.

That, however, represents the generation writ large. Within it are some who, like this year’s 20 in Their Twenties, have already charted their course and jumped in with both feet. This year’s group of high achievers, for instance, is dominated by homeowners, including some working on their second and third properties. You don’t see their successes reflected in much of the hair-on-fire reporting about high housing prices and comparatively high interest rates.

Get them together, as we did on Oct. 14 at Ingram’s, and insights from this diverse group of Kansas City professionals create a portrait of a generation bound together by loyalty, mentorship, and ambition—yet still challenged by limited capital and persistent social divides. Their Kansas City is a place where relationships define careers, where entrepreneurship demands grit, and where civic promise is shadowed by deep-rooted inequities. From corporate boardrooms to startup work spaces, from duplexes to luxury apartments, the city’s story is written in their ambitions, frustrations, and hopes, as well as the peers who call it home.

The Professional Landscape

For corporate professionals, Kansas City offers both stability and constraint. It’s a city where a person can build a lifelong career within a single company—even as conventional wisdom implies multiple employers and career paths for most this age—but where the same close-knit networks that foster trust can stifle mobility.

Trey Taylor, who works for insurance giant Lockton, embodies this duality. “If Lockton takes care of me and I take care of them, I’d like to retire there,” he says. But for those seeking fast-paced advancement, the city can feel small. “If you’re trying to job-hop,” Taylor notes, “Kansas City is not the place to do it.”

He attributes that partly to the business mix—few Fortune 500 headquarters and limited industry churn—but mostly to the social fabric. “So many people know each other and are so intertwined,” he explains. Consider the way word can travel quickly within the business ecosystem. He recalls overhearing a casual conversation at a local restaurant, wherein news about Lockton was being discussed before it had become official—a sign, he says, of how tightly woven the professional community is.

That tightness, though, is also what makes the city’s professional scene unusually supportive. “I’m in printing and publishing,” says Tripp Walsworth, “but I could get a mentor from the insurance or financial industry. Everyone’s connected and looking out for each other.” For professionals willing to leverage the network, guidance and opportunities abound—even across industries.

Mayah Cohen of Virtus echoes that sentiment. “If I left my job today, I could call up 10 people who’d probably find me another,” she says. “It’s all about the relationships you invest in.” Career security here isn’t about a sprawling market of opportunities—it’s about the depth of your social network. In Kansas City, your connections often determine your trajectory more than job boards ever could.

For others, like Ryan Klepper of Block Real Estate Services, loyalty to an established firm carries a sense of legacy. “There’s something to be said for continuing what others built,” he reflects. “It’s not just about creating something new—it’s about honoring that foundation.” That mindset—deep roots over disruption—distinguishes Kansas City’s traditional corporate path from its more volatile entrepreneurial counterpart. In a city that prizes stability, many professionals measure success not by title or salary alone, but by the respect and trust earned over years of mutual investment.

Yet this environment also requires careful navigation. The same bonds that protect careers can create subtle pressures. For newcomers or outsiders, understanding these social currents is crucial. Kansas City’s professional landscape is relational at its core—rewarding those who cultivate loyalty and cautious for those who seek to disrupt.

The Entrepreneurial Frontier

If the city’s corporate world is built on loyalty, its entrepreneurial scene runs on sheer persistence. Founders describe a landscape bursting with ideas but starved for capital.

Cody Isabel, who founded a mental-health tech startup called Mind, Brain and Body Lab, compares Kansas City’s ecosystem with Austin’s. “In Austin, there’s a ton of health tech—I get invited to conventions there all the time,” he says. “Here, it’s challenging. But I want to make it work here.” The draw of local legacy and community, he suggests, can outweigh the financial incentives of moving to larger hubs.

Sam Kulikov, co-founder of e-sports team KC Pioneers and Social Apex Media, has chosen to do the same. “If you’re not willing to put a couple of years into KC, you won’t break anything,” he says. Commitment, not luck, is the entry fee. He highlights the patience required to succeed in an environment where capital is scarce.

James Pyle, who works in private equity at Freedom 3 Capital, outlines a big hurdle: a dearth of institutional investment. “There’s a massive shortage of PE or private credit or special-situations capital in KC,” he says. “There are maybe four or five scaled funds.” Meanwhile, coastal hubs like Chicago and New York attract both money and talent. A not-unimportant consideration: “Those cities are more fun to live in,” he admits. “They pay better, too.”

Capital scarcity shapes everything about the way local founders operate. “We had to go a bit slower,” Kulikov explains. “We siphoned small seed rounds and turned those into profitable investments.” He likens it to mining: “Every entrepreneur here is taking small nuggets and turning them into gold, then raising more to build their mine.”

Yet this constraint also breeds resilience and pride. “We could go to New York, but we’d have no legacy there,” Kulikov says. “Here, we can build one—but we have to earn it.” The challenge of Kansas City entrepreneurship isn’t just survival—it’s the chance to leave a lasting mark on a growing city.

Pyle believes the solution may lie closer to home. “There’s a tremendous amount of family-office capital in Kansas City,” he notes, and it could probably do more to support entrepreneurs and upstart businesses. Isabel adds that other cities are more aggressive in attracting founders, pointing to programs that pay living expenses or offer direct investment. 

For Kulikov, the gap isn’t just financial—it’s cultural. “We beat the drum of entrepreneurship in Kansas City really hard,” he says, “but it’s really, really hard to be an operator” in this ecosystem. Without enough capital, founders end up doing everything themselves, he says: “You’re the janitor, the bookkeeper, the admin, the accountant.”

He believes the city’s future depends on bridging the gap between big corporations and scrappy startups. The story of Kansas City’s entrepreneurial ecosystem is one of tension: ambition constrained by resources, opportunity defined by ingenuity. It’s a place where passion is a prerequisite and perseverance a daily requirement.

The Housing Conundrum

For KCs young professionals, housing is a hurdle that can be navigated, though at times it will challenge one’s creativity. Some view homeownership as a mission; others reject it entirely, as swelling numbers of apartment towers and new complexes will attest.

Trey DeRousse, a commercial real estate professional with Newmark Zimmer, exemplifies the disciplined path. After college, he lived cheaply in a duplex in downtown Lee’s Summit, saving every dollar. When he finally bought a house, he took on two roommates to help cover the mortgage. “They offset my costs and paid down my principal,” he says.

Others got in just before the market turned. “I only got in because of COVID rates,” says Kulikov. “Otherwise, I wouldn’t own a home right now.” Brandan Fitzgerald of Five Elms Capital says he locked in a 2.9 percent mortgage before rates surged, while Meagen Brake of Spring Venture Group used a strategy of flipping a starter home—buying cheap, renovating, and reinvesting profits. “There’s no way I’d be in my current house without doing that twice,” she says. Now, with a low rate and children in a good school district, chances are good that her career remains anchored here. 

For newcomers, the picture is tougher. With mortgage rates hovering near 7 percent, James Pyle advises, “Don’t buy the nice house. Buy the broken-down one.” Mayah Cohen of Virtus is navigating a rent-to-own deal through family friends—a fixer-upper that turned out far worse than expected. “It was way more of a disaster than we thought,” she says. “Time, energy, tears. But it’s still a chance to control something.”

DeRousse and Trey Taylor both highlight the importance of relationships in getting into the market. Taylor negotiated directly with a neighbor to buy without agents. “Start with something rough and work your way up,” he says.

Not everyone, however, wants to play the ownership game. “I love renting,” says Cody Isabel, without hesitation. “It makes more sense to invest in my companies—it returns more.” He relishes the simplicity. “When the washer breaks, I call my landlord. And I get a pool, sauna, gym, and parking.” He points out that ownership’s hidden costs—from down payments to surprise repairs—are often ignored. “Let’s not pretend it’s the same thing,” he says.

Kulikov sees the broader economics shifting. “For years, it was cheaper to own than rent. That’s changing,” he says, anticipating a rental resurgence. He also blames the current stagnation of the housing market on a lack of starter homes. “People aren’t building 1,500-square-foot houses anymore,” he says. “We need those—to get people started.”

The housing discussion underscores a larger theme: adaptability. Young professionals in Kansas City are not just reacting to market conditions—they’re creating strategies that reflect values, risk tolerance, and long-term goals. Whether through shared living, calculated renovations, or deliberate renting, they are navigating a city in flux.

Community and Public Safety

Beyond conversations about careers and housing runs a deeper worry—how Kansas City can assure its younger residents that they will live in a community that is safe, equitable, and whole.

The stories are personal. These pro-fessionals mention personal experiences with break-ins, parking struggles, and fear of even going Downtown after dark. “Not getting your car broken into every weekend,” one says ruefully. Isabel adds, “That happened to me so many times. The Plaza is so sketchy.”

For Mayah Cohen, the experiences were harrowing. “When I first moved here, my car got shot up on the highway,” she says, and more recently, she was at the Chiefs’ 2024 Super Bowl parade when that multiple shooting occurred, claiming one life. Coming here from St. Louis, she understands why others are concerned about the level of gun violence in some parts of the city.

Sam Kulikov offers a broader, more systemic view of crime control. “Our proactive measures are terrible,” he says. “We don’t have the right education system built out for KCMO. KCK is terrible too.” He points to school closures and a stark lack of community infrastructure. “Kansas City, Kan., is known for having more youth-detention centers than basketball courts.”

The problem, he argues, is historical and structural. “We’ve seen the disparity on the east side of the city—we know where it comes from: redlining, zoning, decades of disinvestment.” The city’s east-west divide, long symbolized by Troost Avenue, remains painfully intact. “I asked my parents as a kid why Troost was divided, and they said, ‘It’s just always been that way.’ Twenty years later, it’s worse.”

He warns that without targeted re-investment, the divide will keep widening. “While we sit over in Overland Park with this swell of resources, the east side continues to bleed,” he says. The solution isn’t just money—it’s intentionality. “We need calculated ways to inject capital and opportunity,” he argues. “Teaching people, changing culture, building community—that’s harder than just increasing policing. But without both, the problem only grows.” 

A City’s Choice: Legacy or Leap

Across every conversation, the young professionals describe a city both blessed and burdened by its intimacy. It is a place where connections matter more than titles, where loyalty is currency, and where entrepreneurship is an act of faith.

Its professionals find comfort in the city’s familial business culture, even as they recognize its limits. It’s an entrepreneur’s dream of scaling homegrown ventures, but they face the grind of piecing together small investments. Its young residents chase creative paths to housing or rethink ownership entirely. And beneath it all, its citizens confront the moral weight of a divided city—one still struggling to reconcile prosperity with equity.

Kansas City’s future—and theirs—depends on which instincts prevail: the loyalty that preserves, or the boldness that transforms. If the city can harness both—its deep relational roots and its restless entrepreneurial drive—it may yet write a new legacy: one not just of who you know, but of what you can build together.